Landing a new Onboarding role in 2025: a client case study

I recently had the pleasure of supporting Natalie’s job search. A few weeks ago, she emailed me with the greatest news: she had an offer in hand for an Onboarding role. I’m so grateful she agreed to share her story because I think there is so much to learn from how she approached not just finding a job, but growing her career in Customer Success.

Natalie has worked in Product Support at SaaS companies for several years. A few roles ago, she also managed Onboarding. She liked it a lot, but it had been a few years and she had worked in a few Support roles since. When we met, her question to me was: can I get an onboarding role, with my experience?

Now that she’s about to start her new job, I asked her a few questions about her job search, because I know having just gone through it, she’s got some amazing insight that we can all learn from.

Natalie: Honestly, landing this particular role was influenced by many factors: posting on LinkedIn regularly, targeting the roles I wanted to apply for, applying to jobs early, cold outreaches to hiring managers etc.

That being said, the biggest difference, I think, was that by regularly posting and engaging with content on LinkedIn, my profile was seen by a recruiter. That recruiter was so impressed by my experience, they contacted me first. The conversations continued from there.

My take: Less than 5% of Linkedin users post. Posting is a key advantage in 2025.

Natalie posted about her job search. She posted stories demonstrating her Onboarding skill set. She posted about staying positive and about industry trends. She made herself a magnet for recruiters – it’s no surprise they reached out to her.

But the real differentiator was her mindset. Natalie’s attitude throughout her entire job search was upbeat, relentless. Even in frustrating moments she was unsinkable – always dusting herself off and back at it the next day.

This isn’t just a personality trait, but a skill that can be developed. Rejection is data, not defeat. If you can push past the fear and frustration and rejection and do it anyway, that's the difference between a 3 month search and a 9 month search.

Natalie: The job market today is absolutely crazy. I cannot tell you the amount of times I was rejected for roles I was qualified for. It takes a toll on your mental health. A few years ago with my experience, I'd easily land a new job. The strategies job seekers used previously are just not cutting it, leaving them feeling worn down and defeated.

Once we made some resume tweaks, and I started seeing others on LinkedIn posts about their search, something occurred to me. It wasn't just me. I wasn't alone. Despite everything, I kept pushing. I kept applying to targeted roles. I kept a positive mindset, in addition to what I was already doing. Finally, that perseverance paid off.

My take: Natalie’s experience reflects exactly what I’m tracking across the market. Jobs are getting an overwhelming number of applicants, and are managed by leaner teams than ever before. Strategies that worked in 2023 now feel dated.

Here’s what’s working now: a Targeted, quality job search, built for the madness of today’s market. I outlined the exact strategy Natalie and I used in my guide: How to Job Search in 2025: Quality over Quantity

The breakthrough moment for most of my clients is when they realize they are not being personally rejected, more than likely they aren’t being considered. Once you understand that, you can focus on strategies that help you get in front of hiring teams earlier and proactively.

Natalie: I believe a great Support representative has acquired many skills in that role which translate well to Onboarding. If you are someone who takes on support with an empathetic approach, curiosity mindset, and are passionate about providing white-glove level service, you will absolutely crush it with Onboarding.

My extensive background, namely when it comes to fostering customer relationships, and handling inquiries with care and precision, is what is going to help me excel in an Onboarding role. If you love helping people, and truly enjoy getting to the root cause of the issue, that will take you far. It also helps if you are genuinely easy to get along with. People love to hire those who they can picture themselves working alongside.

My take: One of my specialties is helping Support folks figure out their next move. Support is actually one of the best foundations for Customer Success roles, because Support pros already understand solution selling, finding root causes, and navigating tough customer conversations.

Onboarding is functionally managing customer projects. It requires the ability to scope, meet milestones, and communicate all the way through. Natalie had Onboarding on her resume in the past, but we were also able to position her Support experience in a way that spoke to these critical Onboarding skills.

If you are targeting Success roles, the most critical mindset shift is understanding how you impact revenue. In Support, you likely function as a revenue protector, but I challenge you to think of moments where you saved a customer, or drove an upsell. This is the language of Customer Success. 

Natalie: Working with Nicole was a dream come true. I always had a picture in my head of what a career coach should look like. Let me tell you - Nicole shattered that image in the best possible ways.

From our first conversation, it was abundantly clear to me that not only is Nicole an incredible human being, but she knows her stuff. She has literally walked in my shoes. She went from Support to a Customer Success Manager role to leadership, and now to running her own business helping others navigate these crazy times looking for meaningful work.

She never hesitated to book a call, coach me when I got rejected to see if and where I could improve. Nicole is not only a phenomenal resource for job seekers, but our relationship felt like connecting with an old friend. She would regularly send me jobs I was aligned with, and was one of my biggest cheerleaders, even on days when I just wasn't feeling it. I am so grateful our paths crossed, and have already passed her information along to fellow job seekers. She really is THAT good.

My take: I appreciate Natalie’s kind words, but here’s what really made the difference: my targeted strategy + her ownership of her search.

We strategically positioned Natalie as a capable Onboarding Specialist with a targeted resume, and a recruiter-attracting Linkedin presence. I helped her prepare for interviews with my collection of real Customer Success Interview Questions and frameworks to answer them.

My perspective comes from my time as a hiring manager, as a CSM, as a job seeker, but also as someone reviewing at 280+ Customer Success jobs every month. I speak to hiring managers, recruiters and other coaches so that I am always giving you the most up-to-date answer to the question: what’s working now?

Natalie: Don't give up. I know it sounds tired and cliché. But seriously, don't give up. Believe in yourself. You are highly skilled and qualified and the right opportunity, the one that's meant for you - it will find you. Rejection is just redirection. Don't be afraid to try something new, like messaging a hiring manager on LinkedIn. Sometimes doing something that feels unfamiliar and scary is the key to being seen in this job market. Your win is coming, I just know it.

Natalie was actually the first person to book a Customer Success Clarity Call – and this 45 minute deep dive helped us build the foundation of her job search. Together we analyzed her work history and skills, discussed her career goals, and identified her ideal target role, then built a plan to help position her for an Onboarding role.

In this call, Natalie decided to upgrade to my Customer Success Resume Writing + Linkedin Services.

I wrote Natalie a new resume based on my Customer Success Resume Framework. The biggest transformations were in language and positioning.

For a strategic job search we actually created two resumes to maximize her efforts: a Primary resume optimized for Onboarding roles, and a secondary resume tailored for support roles as a backup strategy. Both versions emphasized her SaaS experience, but had different highlights and language to position her clearly for each role.

Once her resume was application-ready, we transformed her Linkedin profile into a recruiter magnet. This wasn’t just a headline update, but a complete content and positioning overhaul.

When interviews started coming in, we used my Interview prep strategy to prepare her for success.

Why this works: Most job seekers are winging it; applying randomly, hoping something sticks. This systematic approach helps you know exactly what to do, and encourages you to keep going, as each phase builds momentum toward the next.

Natalie went from questioning whether she could get an Onboarding role to an offer at a company that reached out to her. Here’s how the timeline broke down:

In total Natalie interviewed with 5 companies and received 1 offer in about 3 months, 2 months faster than the average job search length.

Natalie’s success combined strategy with mindset into a job search that beat the odds. If you’ve been searching for 3+ months without traction, or getting interviews but no offers, the same strategy can work for you.

The 2025 job market rewards those who understand the new rules. Random applications will leave you frustrated and exhausted. But with the right positioning, targeted strategy, and expert guidance, you can accelerate your timeline significantly.

Natalie’s results came from a comprehensive coaching engagement.

Looking for a more DIY option? Try my Mid-Career CSM Resume Template. Get the exact strategy and process I used create Natalie’s resume for yourself.

Not ready for a call? Start with my free Customer Success Job Search Strategy Guide to learn what’s working for job seekers in 2025.